Sylvatesmin

Base Information

• Chemical Name: Sylvatesmin
• CAS No.: 487-39-8
• Molecular Formula: C21H24 O6
• Molecular Weight: 372.418
• UNII: 886IAL08GN
• DSSTox Substance ID: DTXSID80197588
• Nikkaji Number: J322.966A
• Wikidata: Q27269895
• Metabolomics Workbench ID: 127579
• ChEMBL ID: CHEMBL2260010
• Mol file: 487-39-8.mol

Synonyms:phillygenin

Chemical Property of Sylvatesmin

Chemical Property:

• Vapor Pressure: 4.68E-12mmHg at 25°C
• Melting Point: 133oC
• Boiling Point: 534.9°Cat760mmHg
• PKA: 9.84±0.35(Predicted)
• Flash Point: 277.3°C
• PSA: 66.38000
• Density: 1.225g/cm³
• LogP: 3.49320
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 372.15728848
• Heavy Atom Count: 27
• Complexity: 487

Purity/Quality:

95%-98% ^*data from raw suppliers

Phillygenin 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)[C@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C=C4)O)OC)OC

Technology Process of Sylvatesmin

There total 11 articles about Sylvatesmin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

eudesmine (526-06-7,4375-03-5,16499-02-8,25305-05-9,29106-36-3,38609-26-6,38759-91-0,60102-89-8) → (-)-pinoresinol (81446-29-9) + (+)-pinoresinol monomethyl ether (487-39-8,23397-46-8,23397-47-9,23487-12-9,95404-51-6,29395-87-7) + methylpinoresinol

Guidance literature:

With dipotassium hydrogenphosphate; polypeptone; D-glucose; potassium chloride; magnesium sulfate; iron(II) sulfate; Sucrose; In water; dimethyl sulfoxide; at 25 ℃; for 72h; Yields of byproduct given; Aspergillus niger IFO 4414 presence;

DOI:10.1016/S0031-9422(96)00754-6

Reference yield: 14.1%

(+/-)-dimethylpinoresinol (526-06-7,4375-03-5,16499-02-8,25305-05-9,29106-36-3,38609-26-6,38759-91-0,60102-89-8) → (-)-pinoresinol (81446-29-9) + (+)-pinoresinol monomethyl ether (487-39-8,23397-46-8,23397-47-9,23487-12-9,95404-51-6,29395-87-7) + methylpinoresinol

Guidance literature:

With dipotassium hydrogenphosphate; polypeptone; D-glucose; potassium chloride; magnesium sulfate; iron(II) sulfate; Sucrose; In water; dimethyl sulfoxide; at 25 ℃; for 72h; Yields of byproduct given; Aspergillus niger IFO 4414 presence;

DOI:10.1016/S0031-9422(96)00754-6

Reference yield:

eudesmin (526-06-7,4375-03-5,16499-02-8,25305-05-9,29106-36-3,38609-26-6,38759-91-0,60102-89-8) → pinoresinol (4263-88-1,7452-03-1,10061-38-8,18779-41-4,18779-51-6,24404-50-0,81446-29-9,146338-76-3,487-36-5) + (+)-pinoresinol monomethyl ether (487-39-8,23397-46-8,23397-47-9,23487-12-9,95404-51-6,29395-87-7)

Guidance literature:

In dimethyl sulfoxide; for 24h; biotransformation by aspergillus niger;

DOI:10.1016/S0031-9422(00)90836-7

upstream raw materials:

phillyrin

(3R,4S,5S,6R)-2-{4-[(1S,3aR,4S,6aR)-4-(3,4-Dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-yl]-2-methoxy-phenoxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

eudesmin

eudesmine

Refernces

• 1、 Miyazawa,Kasahara,Kameoka. "Biotransformation of lignans: A specific microbial oxidation of (+)-eudesmin and (+)-magnolin by Aspergillus niger". . p. 1501 - 1507. Retrieved 2007/10/02.
• 2、 Nishibe, Sansei,Tsukamoto, Hiroki,Hisada, Sueo. "Effects of O-Methylation and O-Glucosylation on Carbon-13 Nuclear Magnetic Resonance Chemical Shifts of Matairesinol, (+)-Pinoresinol and (+)-Epipinoresinol". . p. 4653 - 4657. Retrieved 2007/10/02.